(E)-methyl 2-(3-ethoxy-3-oxoprop-1-en-1-yl)-3-fluorobenzoate | 1392227-44-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-methyl 2-(3-ethoxy-3-oxoprop-1-en-1-yl)-3-fluorobenzoate
• 英文别名: methyl 2-[(E)-3-ethoxy-3-oxoprop-1-enyl]-3-fluorobenzoate
• CAS: 1392227-44-9
• 化学式: C₁₃H₁₃FO₄
• 分子量: 252.242
• InChiKey: DAAPNACBXVSUBI-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氟苯甲酸甲酯 、 丙烯酸乙酯 在 silver hexafluoroantimonate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 copper(II) acetate monohydrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以30%的产率得到(E)-methyl 2-(3-ethoxy-3-oxoprop-1-en-1-yl)-3-fluorobenzoate
  参考文献：
  名称：

  Oxidative Alkenylation of Aromatic Esters by Ruthenium-Catalyzed Twofold C–H Bond Cleavages

  摘要：

  Cationic ruthenium(II) complexes enabled catalytic twofold C-H bond functionalizations with weakly coordinating aromatic esters in a highly chemo-, site- and diastereo-selective as well as site selective fashion. The oxidative Fujiwara-Moritani-type alkenylation provided step-economical access to diversely substituted styrenes and proved viable in an aerobic manner. Mechanistic studies were indicative of a reversible acetate-assisted cycloruthenation step.

  DOI：

  10.1021/ol301759v

文献信息

• Oxidative Alkenylation of Aromatic Esters by Ruthenium-Catalyzed Twofold C–H Bond Cleavages
  作者：Karolina Graczyk、Wenbo Ma、Lutz Ackermann

  DOI：10.1021/ol301759v

  日期：2012.8.17

  Cationic ruthenium(II) complexes enabled catalytic twofold C-H bond functionalizations with weakly coordinating aromatic esters in a highly chemo-, site- and diastereo-selective as well as site selective fashion. The oxidative Fujiwara-Moritani-type alkenylation provided step-economical access to diversely substituted styrenes and proved viable in an aerobic manner. Mechanistic studies were indicative of a reversible acetate-assisted cycloruthenation step.